(cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide

Base Information

Chemical Name:(cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide
CAS No.:720678-34-2
Molecular Formula:C₄₂H₆₂O₅Si
Molecular Weight:675.037
Hs Code.:

Synonyms:(cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide

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Chemical Property of (cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide

Chemical Property:

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Technology Process of (cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide

There total 6 articles about (cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

: 181803-16-7
(4R,5R)-tert-butyldiphenylsilyloxyoctan-1-al-5,8-olide

: (4R,5R)-4,5-isopropylidenedioxy-14-pentadecen-1-yl-triphenylphosphonium iodide

: 720678-34-2
(cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide

Guidance literature:: (4R,5R)-4,5-isopropylidenedioxy-14-pentadecen-1-yl-triphenylphosphonium iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 2h;

(4R,5R)-tert-butyldiphenylsilyloxyoctan-1-al-5,8-olide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 20 ℃; for 16h;
DOI:10.1002/chem.200305557

Reference yield:

: 202067-11-6
(4R,5R)-4,5-isopropylidenedioxy-14-en-pentadecanol

: 720678-34-2
(cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 20 °C

2.1: 78 percent / NaHCO₃ / acetonitrile / 16 h / Heating

3.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

3.2: 73 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 16 h / -78 - 20 °C

With 1H-imidazole; iodine; sodium hexamethyldisilazane; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile; 3.1: Wittig coupling;
DOI:10.1002/chem.200305557

Reference yield:

: 202067-20-7
(4R,5R)-1-iodo-4,5-isopropylidenedioxy-14-pentadecene

: 720678-34-2
(cis,4R,5R,12R,13R)-5-tert-butyldiphenylsilyloxytricos-12,13-isopropylidenedioxy-8,22-dien-1,4-olide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 78 percent / NaHCO₃ / acetonitrile / 16 h / Heating

2.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: 73 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 16 h / -78 - 20 °C

With sodium hexamethyldisilazane; sodium hydrogencarbonate; In tetrahydrofuran; acetonitrile; 2.1: Wittig coupling;
DOI:10.1002/chem.200305557